How do you decide whether to upskill an employee in their current role or to reskill them for a new role? The choice depends on the context - the needs of the business and the potential of the employee. Here are scenarios and decision points for each approach:
When to Upskill:
Upskilling is ideal when you want to enhance performance or
advance employees along a familiar path. Typical triggers for
upskilling include:
Technological Updates in Current Role: When new tools, software, or processes are introduced to a job, upskilling helps current job-holders master these changes. For example, the finance team learning a new analytics platform or a factory technician learning to operate an upgraded machine. The role remains fundamentally the same, but requires higher proficiency or new knowledge to stay effective.
Performance Gaps or Growth Opportunities: If an employee has a known skills gap holding them back (e.g., a salesperson lacking advanced negotiation techniques, or a manager needing better coaching skills), targeted upskilling can close that gap. Likewise, if an employee shows potential for greater responsibilities (say, a senior engineer moving toward an architect role), upskilling prepares them for that next level. Essentially, when the question is “how can this person do their job better or take on more?”, upskilling is the answer.
Retention of High Performers: To keep top talent engaged, you may proactively upskill them, offering continuous development (think of it as prepping a successor for leadership, or simply keeping a star employee from stagnating). If the organization anticipates future leadership needs or wants to promote internally, upskilling high performers in leadership, project management, or other advanced skills can be part of succession planning.
When to Reskill:
Reskilling comes into play when roles are changing or being
redefined, or when employees could be more valuable in a different
capacity. Key situations for reskilling include:
Role Redundancy or Transformation: If certain jobs are becoming obsolete due to automation, outsourcing, or strategic shifts, you face a choice: let those employees go, or reskill them for new roles. For example, if a bank reduces its need for manual data entry clerks due to AI software, those clerks might be reskilled into customer support, data analysis, or AI oversight roles. Reskilling is a smart option when you have good people whose current roles won’t exist tomorrow, but who, with training, could fill other critical roles in the organization.
New Business Initiatives: When your organization launches a new product line, service, or enters a new market, you might require skills you don’t currently have in-house. Rather than hiring all new staff, identify employees with adjacent skills and reskill them. Imagine a manufacturing company expanding into IoT (Internet of Things) products - some of its hardware engineers could be reskilled in software programming to support the new product line. This leverages internal experience while adapting to new competency areas.
Organizational Restructuring & Internal Mobility: During restructures or after a merger, roles can shift. You might decide to move people between departments to better match resources to needs - for instance, moving a product expert from a support role into a sales role to leverage their knowledge. This often requires reskilling (in this case, sales training). Anytime employees transition into a significantly different role (even if it’s a “different job within the same company”), a reskilling plan ensures they can quickly acclimate and succeed in their new position.
Preparing for Future Roles (“Talent Redeployment”): Forward-looking companies regularly assess upcoming skill needs. If you foresee, for example, a wave of retirements in a certain function or a future pivot to digital business, you can start reskilling employees now to fill those roles when the time comes. A common scenario is reskilling individual contributors for management roles: a great engineer might be reskilled with people-management and leadership training to take on a supervisor role. In fact, moving from technical work to management is a classic reskill situation - it involves learning a whole new skill set (communication, delegation, etc.) beyond one’s technical expertise.
Make or Buy? A helpful way to decide upskill vs. reskill (or whether to train at all) is the “make or buy” decision in talent management. If the need is for entirely new skills that your current team doesn’t have and you need them immediately, you might consider “buying” talent (hiring from outside). However, hiring is costly and time-consuming, and new hires come with a ramp-up time and cultural adjustment. If you have existing employees who are motivated and capable of learning the new skills, and if you have enough lead time, then “making” talent from within (through reskilling/upskilling) is often the better choice. Essentially:
Opt to reskill/upskill internally when you have people with the potential to grow, and the business can afford the time for them to learn. This is especially true if those employees’ current roles are fading out (so they have bandwidth or urgency to retrain) or if internal knowledge of the company is a valuable asset in the new role.
Opt to hire externally when the skill need is extremely specialized or urgent, or when no one internally is interested or able to learn that skill in the required timeframe. Even then, consider if an external hire could be paired with internal reskilling (for example, hire a subject matter expert to lead a new function and simultaneously reskill some current team members to staff it).
In many cases, the decision isn’t either/or. A balanced strategy might involve both: you reskill a portion of your workforce for new needs and also bring in a few new experts to supplement. The key is to forecast talent needs and plan accordingly - this is where strategic workforce planning and close collaboration between HR and business leaders pays off. When done right, deciding when to upskill vs. reskill ensures you deploy your training resources where they’ll have the greatest impact, and that employees are channeled into roles where they can best contribute and grow.